Woody Allen is considered by many the ultimate actor’s director. Allen is well known for allowing actors the freedom to improvise on set and for shooting long takes without a lot of cutting, giving the actors the ability to play lengthy dialogue scenes with interruption.
Knowing this, many stars take considerably lower salaries to work with Allen, and the result has been a myriad of great acting performances of the years in the films of Woody Allen. Here is a look back at the 15 best acting performances in the films of Woody Allen.
15. Tracey Ullman in “Small Time Crooks” (2000)
Woody is Ray, a career criminal, and Tracey Ullman is his wife, Frenchy. Running a restaurant but hatching a scheme to rob a nearby bank, Ray and Frenchy become rich when Frenchy’s cookies are a huge hit. Now wealthy, Frenchy hires art dealer David (Hugh Grant) to teach the couple how to act in high society, eventually leaving Ray for David and life in Europe.
But after a crooked accountant fleeces the couple of their money, they come back together at the end of the film after Ray tries one last crooked deal that seems to have blown up in his face.
British comedienne Tracey Ullman first came to prominence in her own TV show on the Fox network in the late 1980’s. Her performance as Frenchy in Small Time Crooks was so well received that she was nominated for a Golden Globe Award for Best Actress.
Although only a modest box office success, Small Time Crooks was well liked by critics, who appreciated the film’s wry social commentary. In addition, the witty and intelligent banter between Frenchy and the sometimes dimwitted Ray was highly reminiscent of the characters featured in screwball comedies of the 1930’s and 40’s.
14. Owen Wilson in “Midnight in Paris” (2011)
Wilson is Gil Pender, an unsatisfied screenwriter, on vacation in Paris with his fiancee Inez (Rachel McAdams) and her conservative parents. Getting drunk one night, Gil is picked up by an old fashioned cab filled with characters who identify themselves as icons of the 1920’s, such as F. Scott Fitzgerald, Ernest Hemingway and Josephine Baker.
Returning to meet the same cab each night after midnight, Gil gradually realizes that he is actually being transported back to the jazz age. Eventually the writer decides that it is better to live in the present than the past and, although his relationship with Inez has been destroyed, he seems to have a future in Paris with a new woman who, like Gil, appreciates the writers and artists of the lost generation.
Owen Wilson will never be mistaken for Olivier or Brando, so it’s easy to dismiss his performance in Midnight in Paris as a fluke based on the film’s strong script. His low-key comedic style has been on display in more lightweight films such as Wedding Crashers and Starsky and Hutch, but here he lends exactly the right amount of humor and seriousness to a part that could easily have lapsed into parody.
Midnight in Paris was one of Woody Allen’s most successful movies, and a great deal of that success must be attributed to Owen Wilson’s spot on performance as Gil Pender.
13. Scarlett Johansson in “Match Point” (2005)
After a number of box office failures, Allen hit on the right formula with Match Point, a murder mystery film set in England. Another pass at the themes of crime, guilt and punishment that had informed his earlier films such as Crimes and Misdemeanors and Manhattan Murder Mystery, Match Point features Johansson as the beautiful and alluring Nola Rice, who enters into an affair with Chris Wilton (Jonathan Rhys Meyers).
When Nola becomes pregnant she becomes an inconvenience to Chris, who eventually murders Nola and her neighbor to make it look as if they have been killed during a robbery.
Audiences were very taken with Match Point and with Woody’s use of the lovely Scarlett Johansson as the scorned ‘other woman’ who jeopardizes the position of Chris as son-in-law of the wealthy Hewitt family.
Allen liked Johansson so much that he worked with her again the next year in Scoop (although the film was not well received) and in the much more successful Vicky Christina Barcelona in 2008.
12. Dianne Wiest in “Bullets Over Broadway”
“Don’t Speak!” cries out Helen Sinclair (Dianne Wiest) in Allen’s 1994 film Bullets Over Broadway. John Cusack is David Shayne, an idealistic playwright who finds that he must cast untalented Olive Neal (Jennifer Tilly), the girlfriend of gangster Nick Valenti (Joe Viterelli) who is financing the play.
Eventually Shayne begins to work in the surprisingly brilliant suggestions of Cheech (Chazz Palminteri), who has been assigned by his boss to watch over Olive, into the play. Shayne escapes from the stress of the problematic production by falling into the arms of Helen, an alcoholic and grande dame of the Broadway scene, who comforts the distraught young playwright the best way she knows how.
Wiest had originally received a Best Supporting Actress Academy Award for Allen’s 1986 film Hannah and her Sisters, and she duplicated the feat 8 years later. While Bullets Over Broadway was not a smash hit with audiences, its success with critics and the Academy (Woody received a Best director nomination, and the screenplay was nominated as well) did help Allen reestablish himself after the tabloid scandal of the early 1990’s that he suffered through with Mia Farrow.
11. Javier Bardem in “Vicky Cristina Barcelona”
Vicky (Rebecca Hall) and Cristina (Scarlett Johansson) visit Barcelona for the summer, where they meet artist Juan Antonio (Javier Bardem), who is estranged from his wife María Elena (Penélope Cruz). At first it appears that the carefree Cristina will soon fall in love with Juan Antonio, but through a series of circumstances, the engaged Rebecca first falls under his spell.
Cristina does eventually become involved with the artist, but the two find that their relationship is best balanced out when they are joined by the tempestuous Maria Elena. And though Vicky is now married, she must confront the fact that she may still have feelings for Juan Antonio.
Vicky Cristina Barcelona ended up being one of Allen’s most popular films, grossing nearly 100 million dollars worldwide. Bardem, who had received the Academy Award for Best Supporting Actor a year earlier as the psychotic killer in No Country for Old Men, showed his versatility by playing a completely different part in this offbeat romantic comedy.
He remains thoroughly convincing throughout the film as the artist who finds himself attracted to two American woman, while remaining emotionally connected to his unstable ex-wife.
10. Sean Penn in “Sweet and Lowdown”
A lover of jazz music from the 1930’s and 40’s, Sweet and Lowdown was a longtime project that Woody finally brought to fruition in 1999, with Sean Penn starring as Emmet Ray, a fictional jazz guitarist. Emmet has the talent and chops to be among the best jazz guitarists of all time, even approaching the abilities of his master, Django Reinhardt.
But Ray constantly undermines his own career by his bizarre behavior and heavy drinking, often showing up late for gigs or missing them altogether. In the end, he even undermines his own personal relationship with Hattie (Samantha Morton), the woman he loves, although if we are to believe what we are told in the movie, this loss results in him producing some of his greatest work.
Allen considered playing the part of Ray himself, but in the end he wisely decided to hire the sometimes brilliant Sean Penn to play the part. Penn did not disappoint, giving a great performance which was eventually nominated for an Academy Award for best actor.
Although Sweet and Lowdown was not a hit with audiences, Penn’s performance as the fictional Ray in this pseudo-mockumentary, remains one of the most memorable in any of Woody’s films.
9. Joaquin Phoenix in “Irrational Man”
Professor Abe Lucas (Joaquin Phoenix) arrives to teach at the small New England college of Braylin under the cloud of an existential crisis. Despite his better instincts, he reluctantly begins to date a student, Jill (Emma Stone).
Abe and Jill overhear a woman in a coffee shop complaining about a judge who is treating her unfairly in a custody hearing, and Abe impulsively hatches a plot to kill the judge. When his plan works, Abe’s life surprisingly begins to turn around, until Jill slowly begins to put the pieces together and realize what has happened. She finally confronts Abe with disastrous results.
The character of Abe in Irrational Man was a familiar one for Allen. Haunted by his personal demons and a belief in the meaninglessness of life, Abe appears to be headed nowhere until a sudden twist of fate turns his life around.
A talented actor, Phoenix handled this part with an assuredness that other actors lack and avoided the temptation to turn the role into a simple imitation of Woody Allen, giving a solid performance as a man on the brink.